Chestertown, MD Homes for Sale

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  /19

  $335,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  10578 Tonopah Rd, Chestertown, MD 21620

  Why settle for outdated or overpriced when you can own brand-new construction in a waterfront community just minutes from historic Chestertown? This 3-bed, 2.5-bath Cape Cod in Chesapeake Landing is designed for easy, elegant living—featuring an open floor plan, main-level primary suite with walk-in closet and attached bath, and luxe finishes throughout. Enjoy luxury vinyl plank flooring, granite

  David Moore RE/MAX Executive

  10578 Tonopah Rd, Chestertown, MD 21620
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  /4

  $975,000 Coming Soon

  • 4 Beds
  • 3 Baths
  • 3,401 Sq Ft

  10715 Kasota Rd, Chestertown, MD 21620

  Private waterfront retreat on Mill Creek offering beautiful views, spacious living, and all the peace and quiet you have been looking for. This custom-built Cape-style home is nestled on a serene, protected stretch of water and offers the ideal blend of comfort and tranquility. With 4 bedrooms and 3 full baths, the home features a flexible floor plan designed for both everyday living and

  Sarah King Cross Street Realtors LLC

  10715 Kasota Rd, Chestertown, MD 21620
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  /9

  $699,000 Coming Soon

  • 4 Beds
  • 3.5 Baths
  • 2,008 Sq Ft

  206 S Water St, Chestertown, MD 21620

  See your boat from your house! This historic home located at Chestertown marina has been remodeled as recently as 2021. Gorgeous Heartland appliances compliment the hand crafted free-standing cabinetry in the kitchen. A first floor guest suite addition includes a sitting room connected to the house via a mudroom/porch. Above the mudroom is a second story deck that was built to hold a hot tub

  Beth Ostrander Doug Ashley Realtors, LLC

  206 S Water St, Chestertown, MD 21620
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  /10

  $213,000

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  236 Merganser Dr, Chestertown, MD 21620

  Looking for that off the beaten path property, here it is! Property located in a water privileged community on the Chester River, access at end of road. Investors this property could possibly make a great Airbnb property to add to the portfolio. Home offers a 1/2 acre lot with mature trees. Property backs to Duck Neck Campground. Subject is sold in as is condition, seller nor buyer can make

  Dana Byrd Thurston Wyatt Real Estate, LLC

  236 Merganser Dr, Chestertown, MD 21620
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  /6

  $5,000

  • Land
  • 0.34 Acre
  • $14,706 per Acre

  0 Beltram Rd, Chestertown, MD 21620

  ONLINE AUCTION: Bidding begins 7/15/2025 @ 10:00 AM. Bidding ends 7/17/2025 @ 12:40 PM. List Price is Suggested Opening Bid. 2 Lots available for sale as package in Kent County, MD. on Fish Hatchery Rd, Bunting Rd, Beltram Rd, and Towhee Rd. Call for details. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to Worton Creek Marina, and all the

  Adam Shpritz Ashland Auction Group LLC

  0 Beltram Rd, Chestertown, MD 21620
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  /7

  $5,000

  • Land
  • 0.37 Acre
  • $13,514 per Acre

  0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620

  ONLINE AUCTION: Bidding begins 7/15/2025 @ 10:00 AM. Bidding ends 7/17/2025 @ 12:20 PM. List Price is Suggested Opening Bid. 2 Lots available for sale as package in Kent County, MD. on Fish Hatchery Rd, Bunting Rd, Beltram Rd, and Towhee Rd. Call for details. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown,

  Adam Shpritz Ashland Auction Group LLC

  0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
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  /2

  $10,000

  • Land
  • 0.09 Acre
  • $111,111 per Acre

  0 Texas Ave, Chestertown, MD 21620

  POST AUCTION: MAKE AN OFFER! Lot of land in Tolchester Beach, Maryland located within Kent County. Nearby attractions include Tolchester Marina and +/- 7 miles to all the attractions in Rock Hall, Maryland. Easy Access to Major Traffic Artery Rock Hall Road. Deposit: $5,000.

  Adam Shpritz Ashland Auction Group LLC

  0 Texas Ave, Chestertown, MD 21620
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  /6

  $10,000

  • Land
  • 0.34 Acre
  • $29,412 per Acre

  Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

  POST AUCTION: MAKE AN OFFER! Lot of Land located outside of Chestertown, Maryland within Kent County. Nearby attractions include Warton Creek Marina, Warton Creek, Attractions along Chesapeake Bay, & +/- 7 Miles to downtown Chestertown, Maryland. Easy Access to Major Traffic Artery Fairlee Road. Deposit: $5,000.

  Adam Shpritz Ashland Auction Group LLC

  Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

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